How to tell if you’re reading good writing – David Foster Wallace on books, arguments and how to write a good opening sentence

Once described by John Updike as “just a penis with a thesaurus”, David Foster Wallace has become a quasi-mythical figure in the literary world. The author, essayist and former teacher who told his students “The whole thing [literature] gets very complicated and abstract and hard”, continues to provide inspiration and guidance to book lovers and aspiring writers.

This guidance ranges from the spiritual:

“The really important kind of freedom involves attention, and awareness, and discipline, and effort, and being able truly to care about other people and to sacrifice for them, over and over, in myriad petty little unsexy ways, every day.”

Through to the practical:

“Get a usage dictionary… you need a usage dictionary, you have to be paying a level of attention to your own writing that very few people are doing… A usage dictionary is [like] a linguistic hard drive… For me the big trio is a big dictionary, a usage dictionary, and a thesaurus.”

In so many of Wallace’s words and ideas there is a clear expression of the relationship between the author and language itself – what it means to write, how one should go about the task of writing, and what the writing your produce reflects about your own psychology, and how it helps you to become who you are.

Speaking of books, and the act of reading, Wallace discusses ways you can tell whether what you’re reading is actually any good:

“Reading is a very strange thing. We get talked to about it and talk explicitly about it in first grade and second grade and third grade, and then it all devolves into interpretation. But if you think about what’s going on when you read, you’re processing information at an incredible rate.

One measure of how good the writing is is how little effort it requires for the reader to track what’s going on. For example, I am not an absolute believer in standard punctuation at all times, but one thing that’s often a big shock to my students is that punctuation isn’t merely a matter of pacing or how you would read something out loud. These marks are, in fact, cues to the reader for how very quickly to organize the various phrases and clauses of the sentence so the sentence as a whole makes sense.

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The point where that amount — the amount of time that you’re spending on a sentence, the amount of effort — becomes conscious, when you are conscious that this is hard, is the time when college students’ papers begin getting marked down by the prof.

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One of the things that really good writing does is that it’s able to get across massive amounts of information and various favorable impressions of the communicator with minimal effort on the part of the reader.

That’s why people use terms like flow or effortless to describe writing that they regard as really superb. They’re not saying effortless in terms of it didn’t seem like the writer spent any work. It simply requires no effort to read it — the same way listening to an incredible storyteller talk out loud requires no effort to pay attention. Whereas when you’re bored, you’re conscious of how much effort is required to pay attention.”

A crucial exponent of a good read, Wallace suggests, is a good “opener”. And in his correspondence with Garner he puts down some advice for all aspiring writers on how they should go about writing that often difficult opening sentence:

“A good opener, first and foremost, fails to repel… It’s interesting and engaging. It lays out the terms of the argument, and, in my opinion, should also in some way imply the stakes… If one did it deftly, one could in a one-paragraph opening grab the reader, state the terms of the argument, and state the motivation for the argument. I imagine most good argumentative stuff that I’ve read, you could boil that down to the opener.”

Agreeing with the Aristotelian principles that any good piece of writing should have a beginning, middle and end, Wallace says that while openings can be difficult – it is perhaps the middle that is the toughest nut to crack.

“The middle should work… It lays out the argument in steps, not in a robotic way, but in a way that the reader can tell (a) what the distinct steps or premises of the argument are; and (b), this is the tricky one, how they’re connected to each other. So when I teach nonfiction classes, I spend a disproportionate amount of my time teaching the students how to write transitions, even as simple ones as however and moreover between sentences. Because part of their belief that the reader can somehow read their mind is their failure to see that the reader needs help understanding how two sentences are connected to each other — and also transitions between paragraphs.

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An argumentative writer [should] spend one draft on just the freaking argument, ticking it off like a checklist, and then the real writing part would be weaving it and making the transitions between the parts of the argument — and probably never abandoning the opening, never letting the reader forget what the stakes are here… Never letting the reader think that I’ve lapsed into argument for argument’s sake, but that there’s always a larger, overriding purpose.”

So, saviours of the written word, there you have it! Go out and discover your overriding purposes – and never let them out of your sight!